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I'm trying to ssh to a machine that opens the port 8012 for ssh as opposed to port 22. When I ssh at the command line (ssh -p 8012 username@host), nothing happens. The -vvv option gives no pertinent information other than "trying to connect".

I can do ssh ssh://[email protected] (on standard port 22) without problems.

Further, on this Mac I have a VM running Debian. Within this VM I can ssh on the machine with the non-standard port 8012 without problems.

I also have a separate Windows machine where I also have no problems doing what I described.

Edit: output of ssh -vvv ...:

OpenSSH_8.1p1, LibreSSL 2.7.3
debug1: Reading configuration data /Users/[username]/.ssh/config
debug1: /Users/[username]/.ssh/config line 1: Applying options for *
debug1: Reading configuration data /etc/ssh/ssh_config
debug1: /etc/ssh/ssh_config line 47: Applying options for *
debug1: Connecting to [destination] port 8012.

And then it gets stuck there.

Output of cat ~/.ssh/config:

  AddKeysToAgent yes
  UseKeychain yes
  IdentityFile ~/.ssh/id_rsa

Uncommented lines of the output of cat /etc/ssh/ssh_config:

Host *
    SendEnv LANG LC_*
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  • Assuming you’re not trying to do port forwarding since it’s working on Ubuntu, did you reconfigure sshd_config to listen on port 8012?
    – Allan
    Commented Mar 30, 2020 at 18:30
  • @Allan I don't control the ssh serving machine.
    – screwnut
    Commented Mar 31, 2020 at 8:46
  • If it’s not configured to listen on that port, it’s not going to connect. Did you configure the port in Ubuntu or is it too, something you don’t have control over?
    – Allan
    Commented Mar 31, 2020 at 8:55
  • @Allan Are you talking about the server or my computers? The server is perfectly fine and hundreds of people are connecting to it. I just can't conenct to it from my Mac but I can from a VM within the Mac and from another machine running Windows. My question is really "how can I analyze and debug my problem since it's clearly something wrong with the Mac?"
    – screwnut
    Commented Mar 31, 2020 at 8:58
  • 2
    Are you running 10.15.4 by chance? See mjtsai.com/blog/2020/03/31/macos-10-15-4-broke-ssh, there are some potential workarounds in the comments there. If one of them works for you, please post it as an answer.
    – nohillside ♦
    Commented Apr 1, 2020 at 14:48

1 Answer 1

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It appears my issue is specifically tied to a recent update of MacOS. The answer was found here: https://mjtsai.com/blog/2020/03/31/macos-10-15-4-broke-ssh/. Specifying the IP address of the server rather than its name resolved my issue.

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